Comedian and content creator Druski has credited Drake with transforming his career, pointing to a single opportunity in 2020 as the moment everything shifted.
In a nearly two-hour conversation on The Diary of a CEO with host Steven Bartlett, released on September 24, 2026, Druski (born Drew Desbordes) reflected on the long grind that preceded his mainstream breakthrough. He described years of posting comedy skits with little financial return, living in a room without a mattress after his car was repossessed, and receiving mostly free merchandise or unpaid appearance invites from brands.
The turning point, he said, came when Drake reached out about starring in the music video for “Laugh Now Cry Later,” the 2020 track featuring Lil Durk.
“The thing that changed my life at the time was Drake calling for the ‘Laugh Now Cry Later’ music video,” Druski explained. “Everything shifted after that because brands started to take me seriously. It wasn’t no more sending free merch and ‘Oh, you get this,’ or ‘We’ll bring you out to this event and we just want your appearance and you can get in free.’ Now, it’s transactional with everything.”
He added that real money only began flowing in after the video. “It wasn’t until then that the real money was coming in.”
Directed by Dave Meyers and filmed at Nike’s headquarters in Oregon, the video featured Drake, Lil Durk, and athletes including Kevin Durant, Odell Beckham Jr., and Marshawn Lynch. Druski appeared as the comic relief. The clip has since amassed nearly 600 million views on YouTube.
According to Druski, Drake had already been a fan of his early content, exchanging short messages about the skits. Their relationship progressed when Drake invited him to star in the video. The two had a longer conversation in which Drake spoke about Druski leading “this generation of comedy” and what he represented at the time.
“I’m hearing his words. I’m like, ‘Yo, maybe this dude’s just gassing me up.’ This is wild to hear from somebody who is, in my eyes, a full-blown superstar,” Druski recalled.
He said the impact was nearly immediate. Brands began viewing him as “an actual star” rather than just another comedian, leading to paid partnerships instead of free product or event invites. Druski has repeatedly stated he “could never repay” Drake for taking a chance on him when his content was still relatively early in its development.
“I can’t believe he took a chance on me in that circumstance,” he said. “It shifted everything.”
The discussion formed part of a broader conversation in which Druski dismantled the idea of overnight success. He detailed dropping out of college after realizing comedy was his purpose, surviving an armed robbery that solidified his all-or-nothing commitment to the craft, and later facing repeated rejections from Netflix, Amazon, and FX. Those setbacks prompted him to reinvest brand earnings into self-producing his own projects on YouTube, including the Coulda Been series, which eventually sparked interest and bidding from major platforms.
Druski’s appearance in the “Laugh Now Cry Later” video remains a pivotal early co-sign that helped elevate him from popular Instagram comedian to a mainstream figure with major brand deals, production ventures, and high-profile hosting gigs.
